# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2015acc0004
_database_code_depnum_ccdc_archive 'CCDC 2017941'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;
_audit_creation_date             2021-03-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
pecintas@unex.es
light@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H27 N O11'
_chemical_formula_sum            'C19 H27 N O11'
_chemical_formula_weight         445.41
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.26472(19)
_cell_length_b                   9.99397(19)
_cell_length_c                   10.8624(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.0775(17)
_cell_angle_gamma                90
_cell_volume                     1113.59(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10847
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8960
_cell_measurement_theta_min      1.9660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13739
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.990
_diffrn_reflns_theta_min         1.985
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -112.00   68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000    0.0000  120.0000 180

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00    9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -72.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega  -83.00   68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   18.0000   90.0000 151

#__ type_ start__ end____ width___ exp.time_
  4 omega  -91.00  -28.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -54.0000  -60.0000 63
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0302475000
_diffrn_orient_matrix_UB_12      -0.0242514000
_diffrn_orient_matrix_UB_13      0.0553368000
_diffrn_orient_matrix_UB_21      -0.0619335000
_diffrn_orient_matrix_UB_22      -0.0180120000
_diffrn_orient_matrix_UB_23      0.0217471000
_diffrn_orient_matrix_UB_31      0.0059656000
_diffrn_orient_matrix_UB_32      -0.0642382000
_diffrn_orient_matrix_UB_33      -0.0269884000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage           45.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.889
_reflns_Friedel_fraction_max     0.703
_reflns_number_gt                6143
_reflns_number_total             6383
_reflns_odcompleteness_completeness 93.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.92
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 2385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         6383
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+0.1333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0769
_refine_special_details          
'The OEt group has been refined as split over 2 conformations, as one of these has minor occupancy (<0.15) EADP thermal parameter constraints were applied to split atom pairs.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C19A) = Uanis(C19B)
Uanis(C18A) = Uanis(C18B)
Uanis(O11B) = Uanis(O11A)
3. Others
 Sof(O11B)=Sof(C19B)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C18B)=Sof(H18C)=
 Sof(H18D)=1-FVAR(1)
 Sof(O11A)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(C19A)=Sof(H19A)=Sof(H19B)=
 Sof(H19C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B), C18A(H18A,H18B), C18B(H18C,H18D)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C16(H16A,H16B,H16C),
 C19A(H19A,H19B,H19C), C19B(H19D,H19E,H19F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53430(15) 0.11407(14) 0.21948(12) 0.0408(3) Uani 1 1 d . . . . .
O2 O 0.47111(9) 0.31555(11) 0.14594(9) 0.0205(2) Uani 1 1 d . . . . .
O3 O 0.74418(11) 0.43357(15) 0.21507(13) 0.0354(3) Uani 1 1 d . . . . .
O4 O 0.62829(9) 0.36394(11) 0.37566(10) 0.0229(2) Uani 1 1 d . . . . .
O5 O 0.13099(12) 0.49062(13) 0.05094(11) 0.0318(3) Uani 1 1 d . . . . .
O6 O 0.19888(9) 0.33140(10) 0.18578(9) 0.01828(18) Uani 1 1 d . . . . .
O7 O 0.33449(9) 0.55834(11) 0.42071(10) 0.0228(2) Uani 1 1 d . . . . .
O8 O -0.03905(10) 0.71732(11) 0.25269(10) 0.0217(2) Uani 1 1 d . . . . .
O9 O -0.20136(9) 0.79634(10) 0.36531(9) 0.01994(19) Uani 1 1 d . . . . .
O10 O -0.26721(9) 0.64732(11) 0.55996(10) 0.0220(2) Uani 1 1 d . . . . .
N1 N 0.12044(10) 0.53733(12) 0.34963(11) 0.0171(2) Uani 1 1 d . . . . .
C1 C 0.5832(2) 0.1729(3) 0.01300(17) 0.0468(6) Uani 1 1 d . . . . .
H1A H 0.666952 0.130687 0.022176 0.070 Uiso 1 1 calc R U . . .
H1B H 0.592382 0.257878 -0.027018 0.070 Uiso 1 1 calc R U . . .
H1C H 0.525518 0.117007 -0.035873 0.070 Uiso 1 1 calc R U . . .
C2 C 0.52800(15) 0.19357(17) 0.13741(14) 0.0277(3) Uani 1 1 d . . . . .
C3 C 0.83661(14) 0.27348(17) 0.36003(18) 0.0316(4) Uani 1 1 d . . . . .
H3A H 0.808453 0.182613 0.348390 0.047 Uiso 1 1 calc R U . . .
H3B H 0.849039 0.291329 0.446500 0.047 Uiso 1 1 calc R U . . .
H3C H 0.917306 0.286954 0.319780 0.047 Uiso 1 1 calc R U . . .
C4 C 0.73500(13) 0.36664(16) 0.30594(15) 0.0238(3) Uani 1 1 d . . . . .
C5 C 0.02163(15) 0.27862(19) 0.04941(15) 0.0301(3) Uani 1 1 d . . . . .
H5A H -0.064246 0.312283 0.063042 0.045 Uiso 1 1 calc R U . . .
H5B H 0.034989 0.197031 0.094766 0.045 Uiso 1 1 calc R U . . .
H5C H 0.030551 0.261583 -0.036853 0.045 Uiso 1 1 calc R U . . .
C6 C 0.12069(13) 0.37983(16) 0.09189(12) 0.0212(3) Uani 1 1 d . . . . .
C7 C 0.45435(13) 0.49111(16) 0.45160(14) 0.0238(3) Uani 1 1 d . . . . .
H7A H 0.437947 0.416544 0.506072 0.029 Uiso 1 1 calc R U . . .
H7B H 0.513791 0.552258 0.494353 0.029 Uiso 1 1 calc R U . . .
C8 C 0.51572(12) 0.44017(15) 0.33489(14) 0.0198(3) Uani 1 1 d . . . . .
H8 H 0.541601 0.515256 0.283158 0.024 Uiso 1 1 calc R U . . .
C9 C 0.42014(12) 0.34923(13) 0.26412(12) 0.0162(2) Uani 1 1 d . . . . .
H9 H 0.405534 0.267480 0.311497 0.019 Uiso 1 1 calc R U . . .
C10 C 0.29193(12) 0.42246(14) 0.24111(12) 0.0159(2) Uani 1 1 d . . . . .
H10 H 0.304336 0.499606 0.187097 0.019 Uiso 1 1 calc R U . . .
C11 C 0.24231(11) 0.46825(13) 0.36514(12) 0.0165(2) Uani 1 1 d . . . . .
H11 H 0.231623 0.390526 0.418846 0.020 Uiso 1 1 calc R U . . .
C12 C 0.03574(12) 0.53835(13) 0.43971(12) 0.0164(2) Uani 1 1 d . . . . .
H12 H 0.053529 0.481768 0.506175 0.020 Uiso 1 1 calc R U . . .
C13 C -0.07578(12) 0.61505(13) 0.44414(12) 0.0160(2) Uani 1 1 d . . . . .
C14 C -0.10295(12) 0.71120(13) 0.34504(12) 0.0161(2) Uani 1 1 d . . . . .
C15 C -0.23889(14) 0.88392(15) 0.26312(13) 0.0217(3) Uani 1 1 d . . . . .
H15A H -0.161698 0.913451 0.221927 0.026 Uiso 1 1 calc R U . . .
H15B H -0.282956 0.962303 0.293885 0.026 Uiso 1 1 calc R U . . .
C16 C -0.32818(15) 0.81041(17) 0.17315(15) 0.0289(3) Uani 1 1 d . . . . .
H16A H -0.352180 0.868512 0.105701 0.043 Uiso 1 1 calc R U . . .
H16B H -0.405137 0.782685 0.213851 0.043 Uiso 1 1 calc R U . . .
H16C H -0.284107 0.733178 0.142562 0.043 Uiso 1 1 calc R U . . .
C17 C -0.16169(13) 0.59591(14) 0.54824(13) 0.0195(2) Uani 1 1 d . . . . .
H1 H 0.1067(19) 0.588(2) 0.289(2) 0.027(5) Uiso 1 1 d . . . . .
O11A O -0.10510(12) 0.51450(14) 0.63541(11) 0.0245(3) Uani 0.876(2) 1 d . . P A
1
C18A C -0.18241(16) 0.48613(19) 0.74170(16) 0.0240(3) Uani 0.876(2) 1 d . . P A
1
H18A H -0.225379 0.567487 0.767145 0.029 Uiso 0.876(2) 1 calc R U P A 1
H18B H -0.125322 0.456525 0.809430 0.029 Uiso 0.876(2) 1 calc R U P A 1
C19A C -0.2833(2) 0.3802(2) 0.7140(2) 0.0334(4) Uani 0.876(2) 1 d . . P A 1
H19A H -0.345031 0.412753 0.652542 0.050 Uiso 0.876(2) 1 calc R U P A 1
H19B H -0.327764 0.358977 0.787724 0.050 Uiso 0.876(2) 1 calc R U P A 1
H19C H -0.241568 0.301348 0.683947 0.050 Uiso 0.876(2) 1 calc R U P A 1
O11B O -0.1515(9) 0.4637(11) 0.5949(9) 0.0245(3) Uani 0.124(2) 1 d . . P A 2
C19B C -0.2002(14) 0.4765(15) 0.8134(15) 0.0334(4) Uani 0.124(2) 1 d . . P A 2
H19D H -0.112288 0.449555 0.833958 0.050 Uiso 0.124(2) 1 calc R U P A 2
H19E H -0.257202 0.443338 0.874467 0.050 Uiso 0.124(2) 1 calc R U P A 2
H19F H -0.204918 0.572408 0.810768 0.050 Uiso 0.124(2) 1 calc R U P A 2
C18B C -0.2412(13) 0.4203(15) 0.6889(11) 0.0240(3) Uani 0.124(2) 1 d . . P A 2
H18C H -0.241972 0.323301 0.692925 0.029 Uiso 0.124(2) 1 calc R U P A 2
H18D H -0.328750 0.450239 0.666616 0.029 Uiso 0.124(2) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.194(2) . ?
O2 C2 1.3564(18) . ?
O2 C9 1.4434(15) . ?
O3 C4 1.199(2) . ?
O4 C4 1.3543(17) . ?
O4 C8 1.4403(15) . ?
O5 C6 1.199(2) . ?
O6 C6 1.3635(16) . ?
O6 C10 1.4353(16) . ?
O7 C7 1.4310(16) . ?
O7 C11 1.4244(16) . ?
O8 C14 1.2198(16) . ?
O9 C14 1.3450(15) . ?
O9 C15 1.4545(17) . ?
O10 C17 1.2097(16) . ?
N1 C11 1.4334(15) . ?
N1 C12 1.3323(16) . ?
N1 H1 0.84(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.498(2) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C4 1.502(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C5 C6 1.495(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.524(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.5248(19) . ?
C9 H9 0.9800 . ?
C9 C10 1.5186(17) . ?
C10 H10 0.9800 . ?
C10 C11 1.5276(18) . ?
C11 H11 0.9800 . ?
C12 H12 0.9300 . ?
C12 C13 1.3799(17) . ?
C13 C14 1.4623(18) . ?
C13 C17 1.4714(18) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.507(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O11A 1.3624(18) . ?
C17 O11B 1.418(10) . ?
O11A C18A 1.452(2) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18A C19A 1.504(3) . ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?
O11B C18B 1.465(16) . ?
C19B H19D 0.9600 . ?
C19B H19E 0.9600 . ?
C19B H19F 0.9600 . ?
C19B C18B 1.51(2) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C9 116.17(11) . . ?
C4 O4 C8 118.27(11) . . ?
C6 O6 C10 116.93(11) . . ?
C11 O7 C7 110.79(10) . . ?
C14 O9 C15 115.81(10) . . ?
C11 N1 H1 120.3(14) . . ?
C12 N1 C11 120.49(11) . . ?
C12 N1 H1 118.5(14) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 O2 123.98(14) . . ?
O1 C2 C1 124.73(15) . . ?
O2 C2 C1 111.29(15) . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
O3 C4 O4 124.11(13) . . ?
O3 C4 C3 126.42(14) . . ?
O4 C4 C3 109.47(14) . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
O5 C6 O6 123.21(14) . . ?
O5 C6 C5 125.32(14) . . ?
O6 C6 C5 111.47(13) . . ?
O7 C7 H7A 109.7 . . ?
O7 C7 H7B 109.7 . . ?
O7 C7 C8 109.86(11) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
O4 C8 C7 105.80(11) . . ?
O4 C8 H8 110.5 . . ?
O4 C8 C9 109.52(11) . . ?
C7 C8 H8 110.5 . . ?
C7 C8 C9 109.93(11) . . ?
C9 C8 H8 110.5 . . ?
O2 C9 C8 109.88(10) . . ?
O2 C9 H9 109.9 . . ?
O2 C9 C10 107.81(10) . . ?
C8 C9 H9 109.9 . . ?
C10 C9 C8 109.49(10) . . ?
C10 C9 H9 109.9 . . ?
O6 C10 C9 108.84(11) . . ?
O6 C10 H10 110.3 . . ?
O6 C10 C11 108.73(10) . . ?
C9 C10 H10 110.3 . . ?
C9 C10 C11 108.30(10) . . ?
C11 C10 H10 110.3 . . ?
O7 C11 N1 107.99(10) . . ?
O7 C11 C10 109.00(10) . . ?
O7 C11 H11 109.6 . . ?
N1 C11 C10 110.99(10) . . ?
N1 C11 H11 109.6 . . ?
C10 C11 H11 109.6 . . ?
N1 C12 H12 116.8 . . ?
N1 C12 C13 126.45(12) . . ?
C13 C12 H12 116.8 . . ?
C12 C13 C14 118.40(11) . . ?
C12 C13 C17 118.40(12) . . ?
C14 C13 C17 123.20(11) . . ?
O8 C14 O9 122.17(12) . . ?
O8 C14 C13 122.99(12) . . ?
O9 C14 C13 114.80(11) . . ?
O9 C15 H15A 109.7 . . ?
O9 C15 H15B 109.7 . . ?
O9 C15 C16 109.86(12) . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O10 C17 C13 126.12(13) . . ?
O10 C17 O11A 122.77(13) . . ?
O10 C17 O11B 114.4(4) . . ?
O11A C17 C13 111.07(11) . . ?
O11B C17 C13 111.0(4) . . ?
C17 O11A C18A 115.95(12) . . ?
O11A C18A H18A 109.3 . . ?
O11A C18A H18B 109.3 . . ?
O11A C18A C19A 111.74(16) . . ?
H18A C18A H18B 107.9 . . ?
C19A C18A H18A 109.3 . . ?
C19A C18A H18B 109.3 . . ?
C18A C19A H19A 109.5 . . ?
C18A C19A H19B 109.5 . . ?
C18A C19A H19C 109.5 . . ?
H19A C19A H19B 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C17 O11B C18B 119.1(8) . . ?
H19D C19B H19E 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C18B C19B H19D 109.5 . . ?
C18B C19B H19E 109.5 . . ?
C18B C19B H19F 109.5 . . ?
O11B C18B C19B 110.6(13) . . ?
O11B C18B H18C 109.5 . . ?
O11B C18B H18D 109.5 . . ?
C19B C18B H18C 109.5 . . ?
C19B C18B H18D 109.5 . . ?
H18C C18B H18D 108.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O8 0.84(2) 2.00(2) 2.6267(15) 130.2(18) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C9 C10 O6 66.32(13) . . . . ?
O2 C9 C10 C11 -175.63(10) . . . . ?
O4 C8 C9 O2 -71.85(13) . . . . ?
O4 C8 C9 C10 169.92(10) . . . . ?
O6 C10 C11 O7 179.81(10) . . . . ?
O6 C10 C11 N1 -61.38(13) . . . . ?
O7 C7 C8 O4 -174.81(11) . . . . ?
O7 C7 C8 C9 -56.65(15) . . . . ?
O10 C17 O11A C18A 3.4(2) . . . . ?
O10 C17 O11B C18B -22.6(11) . . . . ?
N1 C12 C13 C14 -3.7(2) . . . . ?
N1 C12 C13 C17 176.20(13) . . . . ?
C2 O2 C9 C8 100.20(14) . . . . ?
C2 O2 C9 C10 -140.54(12) . . . . ?
C4 O4 C8 C7 -145.32(13) . . . . ?
C4 O4 C8 C9 96.24(14) . . . . ?
C6 O6 C10 C9 -138.40(11) . . . . ?
C6 O6 C10 C11 103.83(12) . . . . ?
C7 O7 C11 N1 173.41(11) . . . . ?
C7 O7 C11 C10 -65.92(13) . . . . ?
C7 C8 C9 O2 172.32(11) . . . . ?
C7 C8 C9 C10 54.09(14) . . . . ?
C8 O4 C4 O3 3.7(2) . . . . ?
C8 O4 C4 C3 -176.03(13) . . . . ?
C8 C9 C10 O6 -174.17(10) . . . . ?
C8 C9 C10 C11 -56.12(13) . . . . ?
C9 O2 C2 O1 2.1(2) . . . . ?
C9 O2 C2 C1 -177.02(15) . . . . ?
C9 C10 C11 O7 61.69(13) . . . . ?
C9 C10 C11 N1 -179.50(11) . . . . ?
C10 O6 C6 O5 3.76(19) . . . . ?
C10 O6 C6 C5 -175.47(12) . . . . ?
C11 O7 C7 C8 63.23(15) . . . . ?
C11 N1 C12 C13 170.44(13) . . . . ?
C12 N1 C11 O7 -87.79(15) . . . . ?
C12 N1 C11 C10 152.80(12) . . . . ?
C12 C13 C14 O8 7.6(2) . . . . ?
C12 C13 C14 O9 -170.05(12) . . . . ?
C12 C13 C17 O10 -173.69(14) . . . . ?
C12 C13 C17 O11A 8.55(18) . . . . ?
C12 C13 C17 O11B -27.9(5) . . . . ?
C13 C17 O11A C18A -178.77(13) . . . . ?
C13 C17 O11B C18B -172.6(9) . . . . ?
C14 O9 C15 C16 81.87(15) . . . . ?
C14 C13 C17 O10 6.2(2) . . . . ?
C14 C13 C17 O11A -171.58(13) . . . . ?
C14 C13 C17 O11B 151.9(5) . . . . ?
C15 O9 C14 O8 8.26(19) . . . . ?
C15 O9 C14 C13 -174.04(11) . . . . ?
C17 C13 C14 O8 -172.25(13) . . . . ?
C17 C13 C14 O9 10.07(18) . . . . ?
C17 O11A C18A C19A 79.36(19) . . . . ?
C17 O11B C18B C19B -77.1(13) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PX3RE
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2013acc0123
_database_code_depnum_ccdc_archive 'CCDC 2017937'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;
_audit_creation_date             2021-03-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
light@soton.ac.uk
pecintas@unex.es
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H15 N O7 S'
_chemical_formula_sum            'C12 H15 N O7 S'
_chemical_formula_weight         317.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.6274(4)
_cell_length_b                   9.1304(5)
_cell_length_c                   10.6185(7)
_cell_angle_alpha                92.663(7)
_cell_angle_beta                 99.327(7)
_cell_angle_gamma                90.796(6)
_cell_volume                     728.75(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11964
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12109
_diffrn_reflns_point_group_measured_fraction_full 0.781
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.035
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       XPlain
_diffrn_orient_matrix_UB_11      -0.055744
_diffrn_orient_matrix_UB_12      0.016399
_diffrn_orient_matrix_UB_13      -0.090009
_diffrn_orient_matrix_UB_21      -0.063787
_diffrn_orient_matrix_UB_22      -0.097026
_diffrn_orient_matrix_UB_23      -0.004710
_diffrn_orient_matrix_UB_31      -0.102395
_diffrn_orient_matrix_UB_32      0.048421
_diffrn_orient_matrix_UB_33      0.031732
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.510
_reflns_Friedel_fraction_full    0.564
_reflns_Friedel_fraction_max     0.510
_reflns_number_gt                4803
_reflns_number_total             5042
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1554 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5042
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.1390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0905
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B)
2.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C1B(H1BA,H1BB)
2.c Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C9A(H9AA,H9AB,H9AC), C11A(H11A,H11B,H11C), C7B(H7BA,H7BB,
 H7BC), C9B(H9BA,H9BB,H9BC), C11B(H11D,H11E,H11F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 1.12541(10) 0.49649(9) 1.10616(7) 0.03297(18) Uani 1 1 d . . . . .
O1A O 0.9931(2) 0.4979(2) 0.67634(18) 0.0225(4) Uani 1 1 d . . . . .
O2A O 0.7499(3) 0.5307(2) 0.35170(18) 0.0270(4) Uani 1 1 d . . . . .
O3A O 0.8262(3) 0.7529(3) 0.2901(2) 0.0398(6) Uani 1 1 d . . . . .
O4A O 0.3170(3) 0.5363(3) 0.4178(2) 0.0394(6) Uani 1 1 d . . . . .
O5A O 0.5376(3) 0.6956(2) 0.50253(18) 0.0234(4) Uani 1 1 d . . . . .
O6A O 0.5705(3) 0.8494(2) 0.7898(2) 0.0330(5) Uani 1 1 d . . . . .
O7A O 0.5641(2) 0.6032(2) 0.75907(18) 0.0220(4) Uani 1 1 d . . . . .
N1A N 0.9126(3) 0.5305(3) 0.8743(2) 0.0292(5) Uani 1 1 d . . . . .
C1A C 0.9387(4) 0.4614(3) 0.5423(3) 0.0236(6) Uani 1 1 d . . . . .
H1AA H 0.880399 0.363035 0.530709 0.028 Uiso 1 1 calc R U . . .
H1AB H 1.044204 0.458667 0.498909 0.028 Uiso 1 1 calc R U . . .
C2A C 0.8108(4) 0.5740(3) 0.4833(2) 0.0216(5) Uani 1 1 d . . . . .
H2A H 0.870783 0.672850 0.490237 0.026 Uiso 1 1 calc R U . . .
C3A C 0.6500(4) 0.5787(3) 0.5508(2) 0.0204(5) Uani 1 1 d . . . . .
H3A H 0.583064 0.482803 0.536685 0.024 Uiso 1 1 calc R U . . .
C4A C 0.7135(3) 0.6113(3) 0.6926(2) 0.0195(5) Uani 1 1 d . . . . .
H4A H 0.770831 0.711109 0.707050 0.023 Uiso 1 1 calc R U . . .
C5A C 0.8464(4) 0.4950(3) 0.7431(2) 0.0220(6) Uani 1 1 d . . . . .
H5A H 0.787850 0.395553 0.732754 0.026 Uiso 1 1 calc R U . . .
C6A C 0.7553(4) 0.6358(4) 0.2646(3) 0.0309(7) Uani 1 1 d . . . . .
C7A C 0.6585(5) 0.5815(5) 0.1360(3) 0.0462(10) Uani 1 1 d . . . . .
H7AA H 0.695068 0.481546 0.116914 0.069 Uiso 1 1 calc R U . . .
H7AB H 0.687007 0.645945 0.070515 0.069 Uiso 1 1 calc R U . . .
H7AC H 0.530146 0.581628 0.136672 0.069 Uiso 1 1 calc R U . . .
C8A C 0.3756(4) 0.6598(3) 0.4340(3) 0.0265(6) Uani 1 1 d . . . . .
C9A C 0.2852(4) 0.7939(4) 0.3843(3) 0.0347(7) Uani 1 1 d . . . . .
H9AA H 0.291817 0.869345 0.453768 0.052 Uiso 1 1 calc R U . . .
H9AB H 0.160415 0.769999 0.350221 0.052 Uiso 1 1 calc R U . . .
H9AC H 0.344061 0.830747 0.316216 0.052 Uiso 1 1 calc R U . . .
C10A C 0.5015(4) 0.7326(3) 0.8014(2) 0.0230(5) Uani 1 1 d . . . . .
C11A C 0.3395(4) 0.7081(3) 0.8599(3) 0.0280(6) Uani 1 1 d . . . . .
H11A H 0.234180 0.706439 0.793272 0.042 Uiso 1 1 calc R U . . .
H11B H 0.330184 0.787534 0.923610 0.042 Uiso 1 1 calc R U . . .
H11C H 0.347483 0.614140 0.901276 0.042 Uiso 1 1 calc R U . . .
C12A C 1.0077(4) 0.5093(3) 0.9717(3) 0.0248(6) Uani 1 1 d . . . . .
S1B S 0.06585(10) 0.15795(9) 0.31339(7) 0.0362(2) Uani 1 1 d . . . . .
O1B O 0.4976(2) 0.2381(2) 0.72455(17) 0.0230(4) Uani 1 1 d . . . . .
O2B O 0.4541(3) 0.2135(2) 1.05885(17) 0.0239(4) Uani 1 1 d . . . . .
O3B O 0.4972(3) -0.0146(3) 1.1280(2) 0.0386(5) Uani 1 1 d . . . . .
O4B O -0.0810(3) 0.1658(2) 0.9590(2) 0.0381(5) Uani 1 1 d . . . . .
O5B O 0.1536(2) 0.0310(2) 0.92792(17) 0.0224(4) Uani 1 1 d . . . . .
O6B O 0.0199(3) -0.1213(2) 0.6380(2) 0.0370(5) Uani 1 1 d . . . . .
O7B O 0.0319(2) 0.1242(2) 0.67113(17) 0.0220(4) Uani 1 1 d . . . . .
N1B N 0.3066(3) 0.2055(3) 0.5353(2) 0.0249(5) Uani 1 1 d . . . . .
C1B C 0.5197(4) 0.2751(3) 0.8592(2) 0.0232(6) Uani 1 1 d . . . . .
H1BA H 0.467806 0.372059 0.873465 0.028 Uiso 1 1 calc R U . . .
H1BB H 0.648000 0.281733 0.894806 0.028 Uiso 1 1 calc R U . . .
C2B C 0.4301(4) 0.1607(3) 0.9273(2) 0.0218(5) Uani 1 1 d . . . . .
H2B H 0.486748 0.063388 0.919142 0.026 Uiso 1 1 calc R U . . .
C3B C 0.2333(4) 0.1501(3) 0.8727(2) 0.0209(5) Uani 1 1 d . . . . .
H3B H 0.174311 0.244006 0.891048 0.025 Uiso 1 1 calc R U . . .
C4B C 0.2161(4) 0.1188(3) 0.7289(2) 0.0209(5) Uani 1 1 d . . . . .
H4B H 0.264624 0.020312 0.710588 0.025 Uiso 1 1 calc R U . . .
C5B C 0.3156(4) 0.2378(3) 0.6704(2) 0.0222(6) Uani 1 1 d . . . . .
H5B H 0.264207 0.335939 0.685745 0.027 Uiso 1 1 calc R U . . .
C6B C 0.4944(4) 0.1153(4) 1.1506(3) 0.0285(6) Uani 1 1 d . . . . .
C7B C 0.5367(4) 0.1948(4) 1.2787(3) 0.0385(8) Uani 1 1 d . . . . .
H7BA H 0.658279 0.235283 1.290433 0.058 Uiso 1 1 calc R U . . .
H7BB H 0.526443 0.126441 1.345714 0.058 Uiso 1 1 calc R U . . .
H7BC H 0.453268 0.274640 1.283671 0.058 Uiso 1 1 calc R U . . .
C8B C -0.0034(4) 0.0525(3) 0.9689(3) 0.0249(6) Uani 1 1 d . . . . .
C9B C -0.0625(4) -0.0825(3) 1.0254(3) 0.0303(7) Uani 1 1 d . . . . .
H9BA H -0.093020 -0.159843 0.957968 0.046 Uiso 1 1 calc R U . . .
H9BB H -0.167008 -0.060955 1.065357 0.046 Uiso 1 1 calc R U . . .
H9BC H 0.033685 -0.115282 1.089965 0.046 Uiso 1 1 calc R U . . .
C10B C -0.0519(4) -0.0056(3) 0.6267(3) 0.0248(6) Uani 1 1 d . . . . .
C11B C -0.2379(4) 0.0182(3) 0.5642(3) 0.0293(6) Uani 1 1 d . . . . .
H11D H -0.320537 -0.021719 0.616206 0.044 Uiso 1 1 calc R U . . .
H11E H -0.258557 -0.031652 0.479168 0.044 Uiso 1 1 calc R U . . .
H11F H -0.256940 0.123447 0.556064 0.044 Uiso 1 1 calc R U . . .
C12B C 0.1956(4) 0.1857(3) 0.4430(3) 0.0262(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A C12A 1.568(3) . ?
O1A C1A 1.439(3) . ?
O1A C5A 1.419(3) . ?
O2A C2A 1.435(3) . ?
O2A C6A 1.368(4) . ?
O3A C6A 1.191(4) . ?
O4A C8A 1.202(4) . ?
O5A C3A 1.439(3) . ?
O5A C8A 1.356(3) . ?
O6A C10A 1.203(3) . ?
O7A C4A 1.437(3) . ?
O7A C10A 1.365(3) . ?
N1A C5A 1.423(3) . ?
N1A C12A 1.189(4) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A C2A 1.513(4) . ?
C2A H2A 1.0000 . ?
C2A C3A 1.518(4) . ?
C3A H3A 1.0000 . ?
C3A C4A 1.519(3) . ?
C4A H4A 1.0000 . ?
C4A C5A 1.533(4) . ?
C5A H5A 1.0000 . ?
C6A C7A 1.502(4) . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
C8A C9A 1.490(4) . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10A C11A 1.489(4) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
S1B C12B 1.567(3) . ?
O1B C1B 1.436(3) . ?
O1B C5B 1.413(3) . ?
O2B C2B 1.438(3) . ?
O2B C6B 1.357(4) . ?
O3B C6B 1.200(4) . ?
O4B C8B 1.200(4) . ?
O5B C3B 1.432(3) . ?
O5B C8B 1.353(3) . ?
O6B C10B 1.199(4) . ?
O7B C4B 1.441(3) . ?
O7B C10B 1.366(3) . ?
N1B C5B 1.441(3) . ?
N1B C12B 1.192(4) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C1B C2B 1.514(4) . ?
C2B H2B 1.0000 . ?
C2B C3B 1.519(4) . ?
C3B H3B 1.0000 . ?
C3B C4B 1.525(3) . ?
C4B H4B 1.0000 . ?
C4B C5B 1.528(4) . ?
C5B H5B 1.0000 . ?
C6B C7B 1.496(4) . ?
C7B H7BA 0.9800 . ?
C7B H7BB 0.9800 . ?
C7B H7BC 0.9800 . ?
C8B C9B 1.490(4) . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
C10B C11B 1.489(4) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5A O1A C1A 111.35(19) . . ?
C6A O2A C2A 116.8(2) . . ?
C8A O5A C3A 118.2(2) . . ?
C10A O7A C4A 117.1(2) . . ?
C12A N1A C5A 151.8(3) . . ?
O1A C1A H1AA 109.7 . . ?
O1A C1A H1AB 109.7 . . ?
O1A C1A C2A 110.0(2) . . ?
H1AA C1A H1AB 108.2 . . ?
C2A C1A H1AA 109.7 . . ?
C2A C1A H1AB 109.7 . . ?
O2A C2A C1A 109.1(2) . . ?
O2A C2A H2A 110.2 . . ?
O2A C2A C3A 107.7(2) . . ?
C1A C2A H2A 110.2 . . ?
C1A C2A C3A 109.4(2) . . ?
C3A C2A H2A 110.2 . . ?
O5A C3A C2A 109.0(2) . . ?
O5A C3A H3A 110.3 . . ?
O5A C3A C4A 108.4(2) . . ?
C2A C3A H3A 110.3 . . ?
C2A C3A C4A 108.6(2) . . ?
C4A C3A H3A 110.3 . . ?
O7A C4A C3A 109.0(2) . . ?
O7A C4A H4A 110.1 . . ?
O7A C4A C5A 108.4(2) . . ?
C3A C4A H4A 110.1 . . ?
C3A C4A C5A 109.1(2) . . ?
C5A C4A H4A 110.1 . . ?
O1A C5A N1A 107.5(2) . . ?
O1A C5A C4A 109.5(2) . . ?
O1A C5A H5A 110.3 . . ?
N1A C5A C4A 108.9(2) . . ?
N1A C5A H5A 110.3 . . ?
C4A C5A H5A 110.3 . . ?
O2A C6A C7A 110.1(3) . . ?
O3A C6A O2A 123.6(3) . . ?
O3A C6A C7A 126.3(3) . . ?
C6A C7A H7AA 109.5 . . ?
C6A C7A H7AB 109.5 . . ?
C6A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
O4A C8A O5A 123.4(3) . . ?
O4A C8A C9A 126.4(3) . . ?
O5A C8A C9A 110.3(2) . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
O6A C10A O7A 122.8(3) . . ?
O6A C10A C11A 126.1(3) . . ?
O7A C10A C11A 111.1(2) . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11B 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
N1A C12A S1A 174.0(3) . . ?
C5B O1B C1B 110.3(2) . . ?
C6B O2B C2B 118.3(2) . . ?
C8B O5B C3B 118.6(2) . . ?
C10B O7B C4B 117.3(2) . . ?
C12B N1B C5B 138.2(3) . . ?
O1B C1B H1BA 109.5 . . ?
O1B C1B H1BB 109.5 . . ?
O1B C1B C2B 110.7(2) . . ?
H1BA C1B H1BB 108.1 . . ?
C2B C1B H1BA 109.5 . . ?
C2B C1B H1BB 109.5 . . ?
O2B C2B C1B 105.3(2) . . ?
O2B C2B H2B 110.6 . . ?
O2B C2B C3B 110.0(2) . . ?
C1B C2B H2B 110.6 . . ?
C1B C2B C3B 109.6(2) . . ?
C3B C2B H2B 110.6 . . ?
O5B C3B C2B 109.1(2) . . ?
O5B C3B H3B 110.2 . . ?
O5B C3B C4B 109.2(2) . . ?
C2B C3B H3B 110.2 . . ?
C2B C3B C4B 107.8(2) . . ?
C4B C3B H3B 110.2 . . ?
O7B C4B C3B 109.6(2) . . ?
O7B C4B H4B 110.1 . . ?
O7B C4B C5B 107.0(2) . . ?
C3B C4B H4B 110.1 . . ?
C3B C4B C5B 109.7(2) . . ?
C5B C4B H4B 110.1 . . ?
O1B C5B N1B 106.5(2) . . ?
O1B C5B C4B 109.5(2) . . ?
O1B C5B H5B 110.3 . . ?
N1B C5B C4B 110.0(2) . . ?
N1B C5B H5B 110.3 . . ?
C4B C5B H5B 110.3 . . ?
O2B C6B C7B 109.5(3) . . ?
O3B C6B O2B 123.3(3) . . ?
O3B C6B C7B 127.1(3) . . ?
C6B C7B H7BA 109.5 . . ?
C6B C7B H7BB 109.5 . . ?
C6B C7B H7BC 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
O4B C8B O5B 123.1(3) . . ?
O4B C8B C9B 126.3(3) . . ?
O5B C8B C9B 110.5(3) . . ?
C8B C9B H9BA 109.5 . . ?
C8B C9B H9BB 109.5 . . ?
C8B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
O6B C10B O7B 122.6(3) . . ?
O6B C10B C11B 126.2(3) . . ?
O7B C10B C11B 111.1(2) . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11E 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
N1B C12B S1B 174.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C1A C2A O2A -176.5(2) . . . . ?
O1A C1A C2A C3A -58.8(3) . . . . ?
O2A C2A C3A O5A -67.0(2) . . . . ?
O2A C2A C3A C4A 175.1(2) . . . . ?
O5A C3A C4A O7A 66.8(3) . . . . ?
O5A C3A C4A C5A -175.0(2) . . . . ?
O7A C4A C5A O1A 178.34(18) . . . . ?
O7A C4A C5A N1A -64.4(3) . . . . ?
C1A O1A C5A N1A 179.3(2) . . . . ?
C1A O1A C5A C4A -62.6(3) . . . . ?
C1A C2A C3A O5A 174.52(19) . . . . ?
C1A C2A C3A C4A 56.6(3) . . . . ?
C2A O2A C6A O3A 9.3(4) . . . . ?
C2A O2A C6A C7A -170.1(3) . . . . ?
C2A C3A C4A O7A -175.0(2) . . . . ?
C2A C3A C4A C5A -56.8(3) . . . . ?
C3A O5A C8A O4A 4.4(4) . . . . ?
C3A O5A C8A C9A -175.7(2) . . . . ?
C3A C4A C5A O1A 59.7(3) . . . . ?
C3A C4A C5A N1A 176.9(2) . . . . ?
C4A O7A C10A O6A -3.1(4) . . . . ?
C4A O7A C10A C11A 175.9(2) . . . . ?
C5A O1A C1A C2A 62.5(3) . . . . ?
C6A O2A C2A C1A -131.7(3) . . . . ?
C6A O2A C2A C3A 109.6(3) . . . . ?
C8A O5A C3A C2A 113.0(2) . . . . ?
C8A O5A C3A C4A -129.0(2) . . . . ?
C10A O7A C4A C3A -105.9(2) . . . . ?
C10A O7A C4A C5A 135.5(2) . . . . ?
C12A N1A C5A O1A -57.4(7) . . . . ?
C12A N1A C5A C4A -175.9(6) . . . . ?
O1B C1B C2B O2B -177.3(2) . . . . ?
O1B C1B C2B C3B -59.0(3) . . . . ?
O2B C2B C3B O5B -70.9(3) . . . . ?
O2B C2B C3B C4B 170.7(2) . . . . ?
O5B C3B C4B O7B 68.0(3) . . . . ?
O5B C3B C4B C5B -174.7(2) . . . . ?
O7B C4B C5B O1B 179.6(2) . . . . ?
O7B C4B C5B N1B -63.7(3) . . . . ?
C1B O1B C5B N1B 177.8(2) . . . . ?
C1B O1B C5B C4B -63.3(3) . . . . ?
C1B C2B C3B O5B 173.8(2) . . . . ?
C1B C2B C3B C4B 55.4(3) . . . . ?
C2B O2B C6B O3B -6.1(4) . . . . ?
C2B O2B C6B C7B 172.7(2) . . . . ?
C2B C3B C4B O7B -173.6(2) . . . . ?
C2B C3B C4B C5B -56.3(3) . . . . ?
C3B O5B C8B O4B 1.5(4) . . . . ?
C3B O5B C8B C9B -178.9(2) . . . . ?
C3B C4B C5B O1B 60.7(3) . . . . ?
C3B C4B C5B N1B 177.4(2) . . . . ?
C4B O7B C10B O6B 2.6(4) . . . . ?
C4B O7B C10B C11B -177.2(2) . . . . ?
C5B O1B C1B C2B 63.1(3) . . . . ?
C6B O2B C2B C1B -139.2(2) . . . . ?
C6B O2B C2B C3B 102.8(3) . . . . ?
C8B O5B C3B C2B 135.1(2) . . . . ?
C8B O5B C3B C4B -107.4(2) . . . . ?
C10B O7B C4B C3B -108.7(3) . . . . ?
C10B O7B C4B C5B 132.3(2) . . . . ?
C12B N1B C5B O1B 176.7(4) . . . . ?
C12B N1B C5B C4B 58.1(5) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
